10,549

Oakland, MD Homes

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  • 55 Village Dr Unit 5, Oakland, MD 21550
    55 Village Dr Unit 5, Oakland, MD 21550
    55 Village Dr Unit 5, Oakland, MD 21550
    /45

    $585,000

    $10K PRICE DROP Under Contract
    • 3 Beds
    • 3 Baths
    • 2,280 Sq Ft

    55 Village Dr Unit 5, Oakland, MD 21550

    Tucked in the Yellowstone Village community at Deep Creek Lake, “Dan’s Mountain” is a charming log cabin retreat offering the perfect blend of mountain serenity and convenient access to the area’s top attractions. This 3-bedroom, 3-bathroom home comfortably accommodates guests spanning over 3 levels with a bonus enlcosed porch area. Warm wood interiors and a classic cabin feel welcome you inside,

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    55 Village Dr Unit 5, Oakland, MD 21550
  • 604 #4 E Oak St, Oakland, MD 21550
    604 #4 E Oak St, Oakland, MD 21550
    604 #4 E Oak St, Oakland, MD 21550
    /25

    $2,400 Per Month

    • 2 Beds
    • 1 Bath
    • 3,350 Sq Ft
    • House for Rent

    604 #4 E Oak St, Oakland, MD 21550

    Charming Two-Bedroom Furnish Apartment Ready for short term lease: RecentlyRenovated, Prime Location'Welcome to this beautifully renovated two-bedroom apartment, where modern design meets comfort. Located in a quiet neighborhood, this home is just a short walk from downtown Oakland, offering the perfect blend of convenience and peaceful living.Complete Renovation: Enjoy a fresh and

    Sharon Mokhtari Fairfax Realty of Tysons

    604 #4 E Oak St, Oakland, MD 21550
  • 505 Southern Pines Dr, Oakland, MD 21550
    505 Southern Pines Dr, Oakland, MD 21550
    505 Southern Pines Dr, Oakland, MD 21550
    /38

    $280,000

    Sold Jul 29, 2026

    505 Southern Pines Dr, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft
    • Built 1999

    Last Sold Summary

    • 6% Below List Price
    • $224/SF
    • 124 Days On Market

    Current Estimated Value $290,150

    Last Listing Agent Betsy Spiker Holcomb Taylor-Made Deep Creek Real Estate, LLC

    505 Southern Pines Dr, Oakland, MD 21550
    • Lot 18 Moss Creek Cir, Oakland, MD 21550
      Lot 18 Moss Creek Cir, Oakland, MD 21550
      Lot 18 Moss Creek Cir, Oakland, MD 21550
      /25

      Not Listed For Sale

      Lot 18 Moss Creek Cir, Oakland, MD 21550

      Lot 18 Moss Creek Cir, Oakland, MD 21550

      Last Sold Summary

      • 58 Days On Market

      Last Listing Agent Zach Wesolowski Railey Realty, Inc.

  • 0 Boyd Paugh Ln Unit MDGA2012630, Oakland, MD 21550
    0 Boyd Paugh Ln Unit MDGA2012630, Oakland, MD 21550
    0 Boyd Paugh Ln Unit MDGA2012630, Oakland, MD 21550
    /10

    $1,150,000

    • Land
    • 24,829 Sq Ft
    • $2,017,544 per Acre

    0 Boyd Paugh Ln Unit MDGA2012630, Oakland, MD 21550

    Exceptional 0.57-acre waterfront lot offering approximately 314 feet of shoreline on a quiet point in a protected cove at Deep Creek Lake. The wooded setting provides privacy and an attractive location for your future lake retreat. A Type A dock conveys with the property, and public sewer is available. The parcel is not located within the Heron Cove HOA but has access through the neighborhood by

    Agent Photo

    James Matthews

    Taylor-Made Deep Creek Real Estate, LLC

    0 Boyd Paugh Ln Unit MDGA2012630, Oakland, MD 21550
  • 400 E Alder St Unit 3, Oakland, MD 21550
    400 E Alder St Unit 3, Oakland, MD 21550
    400 E Alder St Unit 3, Oakland, MD 21550
    /29

    $1,550 Per Month

    • 3 Beds
    • 1 Bath
    • 2,312 Sq Ft
    • Condo for Rent

    400 E Alder St Unit 3, Oakland, MD 21550

    Newly renovated second floor apartment with 3 bedrooms freshly painted, with new floors and a fully renovated bathroom. The apartment boasts high ceilings and charming original fixtures. Located in the heart of downtown its within walking distance of shops and restaurants!

    Sharon Mokhtari Fairfax Realty of Tysons

    400 E Alder St Unit 3, Oakland, MD 21550
  • 1989 Lake Shore Dr, Oakland, MD 21550
    1989 Lake Shore Dr, Oakland, MD 21550
    1989 Lake Shore Dr, Oakland, MD 21550
    /76

    $1,400,000

    Sold Dec 04, 2025

    1989 Lake Shore Dr, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 3,008 Sq Ft
    • Built 1964

    Last Sold Summary

    • $465/SF
    • 18 Days On Market

    Current Estimated Value $1,507,407

    Last Listing Agent Justin Liller Railey Realty, Inc.

    1989 Lake Shore Dr, Oakland, MD 21550
    • 20160 Garrett Hwy Unit H712, Oakland, MD 21550
      20160 Garrett Hwy Unit H712, Oakland, MD 21550
      20160 Garrett Hwy Unit H712, Oakland, MD 21550
      /28

      Not Listed For Sale

      20160 Garrett Hwy Unit H712, Oakland, MD 21550

      • 1 Bed
      • 1 Bath
      • 450 Sq Ft
      • Built 1972
      20160 Garrett Hwy Unit H712, Oakland, MD 21550

      Last Sold Summary

      • 124 Days On Market

      Last Listing Agent Larry Smith Railey Realty, Inc.

  • 660 Glendale Rd, Oakland, MD 21550
    660 Glendale Rd, Oakland, MD 21550
    660 Glendale Rd, Oakland, MD 21550
    /62

    $999,000

    $301K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,592 Sq Ft

    660 Glendale Rd, Oakland, MD 21550

    Welcome to 660 Glendale Road — a luxury, mountain-chalet log home in the heart of Deep Creek Lake. This well appointed 5-bedroom, 3-bath home offers nearly 2,600 square feet of thoughtfully upgraded living space designed for lake life at its best. Enjoy lake views with western exposure on the expansive wraparound decks on main and lower levels. Many recent upgrades including roof, decks, covered

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    660 Glendale Rd, Oakland, MD 21550
  • 604 E Oak St, Oakland, MD 21550
    604 E Oak St, Oakland, MD 21550
    604 E Oak St, Oakland, MD 21550
    /20

    $1,990 Per Month

    • 3 Beds
    • 1 Bath
    • 3,350 Sq Ft
    • House for Rent

    604 E Oak St, Oakland, MD 21550

    Charming Three-Bedroom Apartment Recently Renovated, Prime Location'Welcome to this beautifully renovated three-bedroom apartment, where modern design meets comfort. Located in a quiet neighborhood, this home is just a short walk from downtown Oakland, offering the perfect blend of convenience and peaceful living.Complete Renovation: Enjoy a fresh and stylish space with all-new finishes,

    Sharon Mokhtari Fairfax Realty of Tysons

    604 E Oak St, Oakland, MD 21550
  • 11 Sunset Dr, Oakland, MD 21550
    11 Sunset Dr, Oakland, MD 21550
    11 Sunset Dr, Oakland, MD 21550
    /42

    $270,000

    Sold Nov 21, 2025

    11 Sunset Dr, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 2000

    Last Sold Summary

    • $193/SF
    • 29 Days On Market

    Current Estimated Value $282,691

    Last Listing Agent Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    11 Sunset Dr, Oakland, MD 21550
    • 612 Harvey Winters Dr, Oakland, MD 21550
      612 Harvey Winters Dr, Oakland, MD 21550
      612 Harvey Winters Dr, Oakland, MD 21550
      /70

      Est $489,972

      Not Listed For Sale

      612 Harvey Winters Dr, Oakland, MD 21550

      • 4 Beds
      • 3 Baths
      • 2,473 Sq Ft
      • Built 2010
      612 Harvey Winters Dr, Oakland, MD 21550

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Zach Wesolowski Railey Realty, Inc.

  • 22 Shady Hill Dr, Oakland, MD 21550
    22 Shady Hill Dr, Oakland, MD 21550
    22 Shady Hill Dr, Oakland, MD 21550
    /55

    $210,000

    Under Contract
    • 2 Beds
    • 1 Bath
    • 1,056 Sq Ft

    22 Shady Hill Dr, Oakland, MD 21550

    Tucked away in a peaceful, nature-filled setting, this charming 2-bedroom, 1-bath ranch offers comfortable one-level living with a truly unique atmosphere. Surrounded by colorful wildflowers and mature landscaping, the property provides a quiet retreat that's perfect for enjoying the outdoors. Inside, the home has seen several recent upgrades, making it move-in ready while maintaining its

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    22 Shady Hill Dr, Oakland, MD 21550
  • 3472 Lake Shore Dr, Oakland, MD 21550
    3472 Lake Shore Dr, Oakland, MD 21550
    3472 Lake Shore Dr, Oakland, MD 21550
    /76

    $775,000

    Sold Aug 25, 2025

    3472 Lake Shore Dr, Oakland, MD 21550

    • 5 Beds
    • 5.5 Baths
    • 2,904 Sq Ft
    • Built 2007

    Last Sold Summary

    • $267/SF
    • 112 Days On Market

    Current Estimated Value $824,967

    Last Listing Agent Betsy Spiker Holcomb Taylor-Made Deep Creek Real Estate, LLC

    3472 Lake Shore Dr, Oakland, MD 21550
    • 4960 Hutton Rd, Oakland, MD 21550
      4960 Hutton Rd, Oakland, MD 21550
      4960 Hutton Rd, Oakland, MD 21550
      /32

      Est $151,021

      Not Listed For Sale

      4960 Hutton Rd, Oakland, MD 21550

      • 2 Beds
      • 1 Bath
      • 1,080 Sq Ft
      • Built 1971
      4960 Hutton Rd, Oakland, MD 21550

      Last Sold Summary

      • 205 Days On Market

      Last Listing Agent Justin Liller Railey Realty, Inc.

  • 180 Paradise Ridge Rd, Oakland, MD 21550
    180 Paradise Ridge Rd, Oakland, MD 21550
    180 Paradise Ridge Rd, Oakland, MD 21550
    /51

    $689,000

    • 4 Beds
    • 3 Baths
    • 2,402 Sq Ft

    180 Paradise Ridge Rd, Oakland, MD 21550

    Experience the best of Deep Creek Lake living at this beautifully renovated mountain retreat in the peaceful and desirable Paradise Ridge lake access community. Thoughtfully updated from top to bottom, this home blends modern comfort with the serenity of nature, creating the perfect full-time residence, vacation getaway, or potential vacation rental investment property. One of the property's

    Agent Photo

    Brian Homberg

    Taylor-Made Deep Creek Real Estate, LLC

    180 Paradise Ridge Rd, Oakland, MD 21550
  • Lot 15 Little Mountain Rd, Oakland, MD 21550
    Lot 15 Little Mountain Rd, Oakland, MD 21550
    Lot 15 Little Mountain Rd, Oakland, MD 21550
    /9

    $23,000

    Sold Nov 03, 2025

    Lot 15 Little Mountain Rd, Oakland, MD 21550

    • Land
    • 2.71 Acres
    • $8,487 per Acre

    Last Sold Summary

    • 34% Below List Price
    • 132 Days On Market

    Last Listing Agent ADAM MURRAY BERKSHIRE HATHAWAY HOMESERVICES TOUCHDOWN HOME PROS REALTY

    Lot 15 Little Mountain Rd, Oakland, MD 21550
    • 343 Maple Del Ln, Oakland, MD 21550
      343 Maple Del Ln, Oakland, MD 21550
      343 Maple Del Ln, Oakland, MD 21550
      /47

      Est $425,386

      Not Listed For Sale

      343 Maple Del Ln, Oakland, MD 21550

      • 3 Beds
      • 2.5 Baths
      • 1,404 Sq Ft
      • Built 1993
      343 Maple Del Ln, Oakland, MD 21550

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Julie Mead The KW Collective

  • 211 High Point Ridge Rd, Oakland, MD 21550
    211 High Point Ridge Rd, Oakland, MD 21550
    211 High Point Ridge Rd, Oakland, MD 21550
    /99

    $1,350,000

    $145K PRICE DROP Under Contract
    • 4 Beds
    • 3.5 Baths
    • 3,472 Sq Ft

    211 High Point Ridge Rd, Oakland, MD 21550

    Once in a lifetime opportunity to own one of Maryland’s most distinctive homes. Built in 2019, this fully custom modern home is located on the highest elevation building lot in the state of Maryland, making it the highest elevation home in the state at over 3300 feet above sea level. Designed to take full advantage of the setting, the property offers incredible panoramic views stretching across

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    211 High Point Ridge Rd, Oakland, MD 21550
  • 1589 Lake Shore Dr, Oakland, MD 21550
    1589 Lake Shore Dr, Oakland, MD 21550
    1589 Lake Shore Dr, Oakland, MD 21550
    /62

    $1,399,000

    Sold Sep 05, 2025

    1589 Lake Shore Dr, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • 1,872 Sq Ft
    • Built 2020

    Last Sold Summary

    • $747/SF
    • 3 Days On Market

    Current Estimated Value $1,499,645

    Last Listing Agent Betsy Spiker Holcomb Taylor-Made Deep Creek Real Estate, LLC

    1589 Lake Shore Dr, Oakland, MD 21550
    • 414 D St, Oakland, MD 21550
      414 D St, Oakland, MD 21550
      414 D St, Oakland, MD 21550
      /45

      Est $155,321

      Not Listed For Sale

      414 D St, Oakland, MD 21550

      • 2 Beds
      • 1 Bath
      • 936 Sq Ft
      • Built 1950
      414 D St, Oakland, MD 21550

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Michelle Clark Taylor-Made Deep Creek Real Estate, LLC

  • 0 3 15 Acres Woodlands Hill Dr Unit MDGA2012042, Oakland, MD 21550
    0 3 15 Acres Woodlands Hill Dr Unit MDGA2012042, Oakland, MD 21550
    0 3 15 Acres Woodlands Hill Dr Unit MDGA2012042, Oakland, MD 21550
    /3

    $200,000

    • Land
    • 3.15 Acres
    • $63,492 per Acre

    0 3 15 Acres Woodlands Hill Dr Unit MDGA2012042, Oakland, MD 21550

    3.15 unrestricted acres in the heart of Deep Creek Lake area, only 1/4 mile away from the lake. Ready to build your dream home with seclusion and privacy, close to area parks and amenities. No HOA.

    Agent Photo

    Brian Homberg

    Taylor-Made Deep Creek Real Estate, LLC

    0 3 15 Acres Woodlands Hill Dr Unit MDGA2012042, Oakland, MD 21550
  • 17 Driftwood Ln, Oakland, MD 21550
    17 Driftwood Ln, Oakland, MD 21550
    17 Driftwood Ln, Oakland, MD 21550
    /73

    $305,000

    Sold Nov 06, 2025

    17 Driftwood Ln, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 2,092 Sq Ft
    • Built 1978

    Last Sold Summary

    • $146/SF
    • 113 Days On Market

    Current Estimated Value $293,353

    Last Listing Agent Larry Smith Railey Realty, Inc.

    17 Driftwood Ln, Oakland, MD 21550
    • 723 E Oak St, Oakland, MD 21550
      723 E Oak St, Oakland, MD 21550
      723 E Oak St, Oakland, MD 21550
      /43

      Est $168,148

      Not Listed For Sale

      723 E Oak St, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 988 Sq Ft
      • Built 1966
      723 E Oak St, Oakland, MD 21550

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Kevin Liller Railey Realty, Inc.

  • 20160 Garrett Hwy Unit H706, Oakland, MD 21550
    20160 Garrett Hwy Unit H706, Oakland, MD 21550
    20160 Garrett Hwy Unit H706, Oakland, MD 21550
    /27

    $309,000

    • 1 Bed
    • 1 Bath
    • 550 Sq Ft

    20160 Garrett Hwy Unit H706, Oakland, MD 21550

    Welcome to Will O' the Wisp Unit H706, a beautiful top-floor lakefront condo offering some of the most breathtaking views of Deep Creek Lake. Perched on the 7th floor and overlooking one of the lake's widest sections, this fully furnished two-level condo features 1 bedroom, 1 bath, and 550 square feet of comfortable, low-maintenance living - ideal as a vacation retreat, year-round getaway, or

    Agent Photo

    James Matthews

    Taylor-Made Deep Creek Real Estate, LLC

    20160 Garrett Hwy Unit H706, Oakland, MD 21550
  • 627 Hamill St, Oakland, MD 21550
    627 Hamill St, Oakland, MD 21550
    627 Hamill St, Oakland, MD 21550
    /47

    $180,000

    Sold Nov 24, 2025

    627 Hamill St, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,322 Sq Ft
    • Built 1886

    Last Sold Summary

    • $136/SF
    • 2 Days On Market

    Current Estimated Value $189,828

    Last Listing Agent Rich Orr Railey Realty, Inc.

    627 Hamill St, Oakland, MD 21550
    • 500 Seneca Ave, Oakland, MD 21550
      500 Seneca Ave, Oakland, MD 21550
      500 Seneca Ave, Oakland, MD 21550
      /13

      Est $107,898

      Not Listed For Sale

      500 Seneca Ave, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 1,284 Sq Ft
      • Built 1940
      500 Seneca Ave, Oakland, MD 21550

      Last Sold Summary

      • 577 Days On Market

      Last Listing Agent Paul Macy Garrett Land Sales, PC

  • Lot 2 Cedar Ln, Oakland, MD 21550
    Lot 2 Cedar Ln, Oakland, MD 21550
    Lot 2 Cedar Ln, Oakland, MD 21550
    /16

    $35,000

    $15K PRICE DROP
    • Land
    • 26,136 Sq Ft
    • $58,333 per Acre

    Lot 2 Cedar Ln, Oakland, MD 21550

    Cleared, perc approved and ready to build! Lot 2 Cedar Lane sits on a 0.6 acre level lot at the beginning of Cedar Lane which sits close to the community center, tennis courts, pavilion and only a short ride to Muddy Creek and the access to Youghiogheny River! Youghiogheny Mountain Resort offers over 50 miles of trails for riding ATV’s, side by sides, fishing at Muddy Creek and much more! The

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    Lot 2 Cedar Ln, Oakland, MD 21550
  • Lot 5A Valley Rd, Oakland, MD 21550
    Lot 5A Valley Rd, Oakland, MD 21550
    Lot 5A Valley Rd, Oakland, MD 21550
    /14

    $17,000

    Sold Dec 18, 2025

    Lot 5A Valley Rd, Oakland, MD 21550

    • Land
    • 2.45 Acres
    • $6,939 per Acre

    Last Sold Summary

    • 1,047 Days On Market

    Last Listing Agent Nick Fratz-Orr Railey Realty, Inc.

    Lot 5A Valley Rd, Oakland, MD 21550
    • 10 Laurel Brook Dr, Oakland, MD 21550
      10 Laurel Brook Dr, Oakland, MD 21550
      10 Laurel Brook Dr, Oakland, MD 21550
      /39

      Est $218,489

      Not Listed For Sale

      10 Laurel Brook Dr, Oakland, MD 21550

      • 2 Beds
      • 2 Baths
      • Built 1989
      10 Laurel Brook Dr, Oakland, MD 21550

      Last Sold Summary

      • 421 Days On Market

      Last Listing Agent Michael Cumerlato Jason Mitchell Group

  • 0 5 Acres Lake Shore Dr, Oakland, MD 21550
    0 5 Acres Lake Shore Dr, Oakland, MD 21550
    0 5 Acres Lake Shore Dr, Oakland, MD 21550
    /3

    $250,000

    • Land
    • 5 Acres
    • $50,000 per Acre

    0 5 Acres Lake Shore Dr, Oakland, MD 21550

    5.0 unrestricted acres in the heart of Deep Creek Lake area, only 1/4 mile away from the lake. Ready to build your dream home with seclusion and privacy, close to area parks and amenities.

    Agent Photo

    Brian Homberg

    Taylor-Made Deep Creek Real Estate, LLC

    0 5 Acres Lake Shore Dr, Oakland, MD 21550
  • 366 Glendale Rd, Oakland, MD 21550
    366 Glendale Rd, Oakland, MD 21550
    366 Glendale Rd, Oakland, MD 21550
    /29

    $369,900

    Sold Oct 17, 2025

    366 Glendale Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,392 Sq Ft
    • Built 1997

    Last Sold Summary

    • $266/SF
    • 152 Days On Market

    Current Estimated Value $372,891

    Last Listing Agent Adam Belasco Keller Williams Capital Properties

    366 Glendale Rd, Oakland, MD 21550
    • 1220 Broadford Rd, Oakland, MD 21550
      1220 Broadford Rd, Oakland, MD 21550
      1220 Broadford Rd, Oakland, MD 21550
      /52

      Est $392,819

      Not Listed For Sale

      1220 Broadford Rd, Oakland, MD 21550

      • 4 Beds
      • 2.5 Baths
      • 2,092 Sq Ft
      • Built 1971
      1220 Broadford Rd, Oakland, MD 21550

      Last Sold Summary

      • 58 Days On Market

      Last Listing Agent Nina Beitzel Railey Realty, Inc.

  • 59 Boyd Paugh Ln, Oakland, MD 21550
    59 Boyd Paugh Ln, Oakland, MD 21550
    59 Boyd Paugh Ln, Oakland, MD 21550
    /81

    $2,150,000

    Open Sat 11AM - 2PM $950K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 4,200 Sq Ft

    59 Boyd Paugh Ln, Oakland, MD 21550

    Rare opportunity to own a truly exceptional Deep Creek Lake property. The custom 5-bedroom, 3.5-bath lakefront home is situated on a beautifully landscaped and wooded 0.88-acre lot with approximately 209 feet of shoreline. Features include a main-level primary suite with dressing area, spacious kitchen and great room, cathedral ceilings, recreation room with built-in bar, screened porch, generous

    Agent Photo

    James Matthews

    Taylor-Made Deep Creek Real Estate, LLC

    59 Boyd Paugh Ln, Oakland, MD 21550
  • 0 Upperman Rd Unit MDGA2010944, Oakland, MD 21550
    0 Upperman Rd Unit MDGA2010944, Oakland, MD 21550
    0 Upperman Rd Unit MDGA2010944, Oakland, MD 21550
    /4

    $250,000

    Sold Feb 05, 2026

    0 Upperman Rd Unit MDGA2010944, Oakland, MD 21550

    • Land
    • 45.7 Acres
    • $5,470 per Acre

    Last Sold Summary

    • 23% Below List Price
    • 0 Days On Market

    Last Listing Agent Russell Bounds Railey Realty, Inc.

    0 Upperman Rd Unit MDGA2010944, Oakland, MD 21550
    • 1100 S Blakeslee Rd, Oakland, MD 21550
      1100 S Blakeslee Rd, Oakland, MD 21550
      1100 S Blakeslee Rd, Oakland, MD 21550
      /127

      Est $2,771,247

      Not Listed For Sale

      1100 S Blakeslee Rd, Oakland, MD 21550

      • 5 Beds
      • 5.5 Baths
      • 6,572 Sq Ft
      • Built 1998
      1100 S Blakeslee Rd, Oakland, MD 21550

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Bill Weissgerber Railey Realty, Inc.

  • Lot 13 Dogwood Dr, Oakland, MD 21550
    Lot 13 Dogwood Dr, Oakland, MD 21550
    Lot 13 Dogwood Dr, Oakland, MD 21550
    /21

    $22,500

    • Land
    • 25,264 Sq Ft
    • $38,793 per Acre

    Lot 13 Dogwood Dr, Oakland, MD 21550

    Discover the perfect blend of privacy and potential with these two adjoining lots located in the Youghiogheny Mountain Resort community. Lot 13 Dogwood Drive offers 0.58 wooded acres of mountain serenity. Lot 13 is approved for a sand mound septic system, making it an ideal site for your future mountain cabin or getaway retreat. The community offers gated access, over 50 miles of community roads

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    Lot 13 Dogwood Dr, Oakland, MD 21550
  • 0 N Hammond St, Oakland, MD 21550
    0 N Hammond St, Oakland, MD 21550
    /2

    $20,000

    Sold Mar 03, 2026

    0 N Hammond St, Oakland, MD 21550

    • Land
    • 20,908 Sq Ft
    • $41,667 per Acre

    Last Sold Summary

    • 33% Below List Price
    • 6 Days On Market

    Last Listing Agent Betsy Spiker Holcomb Taylor-Made Deep Creek Real Estate, LLC

    0 N Hammond St, Oakland, MD 21550
    • 462 Skippers Point Rd, Oakland, MD 21550
      462 Skippers Point Rd, Oakland, MD 21550
      462 Skippers Point Rd, Oakland, MD 21550
      /66

      Est $549,684

      Not Listed For Sale

      462 Skippers Point Rd, Oakland, MD 21550

      • 5 Beds
      • 2 Baths
      • 1,620 Sq Ft
      • Built 1983
      462 Skippers Point Rd, Oakland, MD 21550

      Last Sold Summary

      • 51 Days On Market

      Last Listing Agent Dale Carpenter Railey Realty, Inc.

  • 122 Woodlands Hill Ln, Oakland, MD 21550
    122 Woodlands Hill Ln, Oakland, MD 21550
    122 Woodlands Hill Ln, Oakland, MD 21550
    /59

    $1,200,000

    • 4 Beds
    • 4.5 Baths
    • 2,656 Sq Ft

    122 Woodlands Hill Ln, Oakland, MD 21550

    Outdoor lovers retreat! Wooded trails and wildlife - HUNTING ALLOWED with no HOA restrictions. Welcome to mountain and lake living at its finest. Nestled on 6.89 very private acres, 122 Woodlands Hill Lane offers the perfect blend of seclusion, space, and comfort in one of Garrett County’s most desirable settings in the heart of Deep Creek Lake. This impressive 4-bedroom, 4.5-bath home features

    Agent Photo

    Brian Homberg

    Taylor-Made Deep Creek Real Estate, LLC

    122 Woodlands Hill Ln, Oakland, MD 21550

Showing Results 1 - 40, Page 1 of 18

Maryland Garrett County

Real Estate & Homes

Home Prices in Oakland, MD

The median home sale price in Oakland, MD is $422,500, up 5% year-over-year. Homes in Oakland sell in 96 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price
$422,500
Median Single Family Sale Price
$420,000
Median Townhouse Sale Price
$462,450
Median 2 Bedroom Sale Price
$294,000
Median 1 Bedroom Sale Price
$224,900
Average Price Per Sq Ft
$276
Number of Homes for Sale
57
Last 12 months Home Sales
142
Months of Supply
4.80
Median List Price
$425,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
5%
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